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Hello, and welcome to my first case study in a long time!

I’ll be sharing the branding design process for a fun project I completed in 2020. They say design is a series of compromises, so I want to show you everything including where I ended up being wrong and what didn’t make it into the final branding.

For context

This project was for a digital marketing company called Lonely Captain. They’ve been around for a while—they actually first told me about their desire to rebrand in 2015—and started as a freelance operation, hence the name. They found success and grew the company.

I mentioned the year 2015, but it wasn’t until 2019 when the CEO had a speaking engagement & booth at a big event that they pulled the trigger on redesigning. We couldn’t complete a full website in time, so we decided to launch with a “coming soon” countdown-style page to build anticipation.

My initial thoughts on the project

  • How do we play with the “sad” theme of the name while staying professional?
  • How can I design the brand so another designer could easily pick it up and run with it? (This company hires a lot of freelancers.)
  • The company’s partners include Google and Ahrefs. With such big names, how can I help them fit into that niche but at the same time stand out?

Starting with the brand personality

Determining the brand personality was a mixture of two steps: a questionnaire to learn about the company’s ideal client and figuring out what universal personality archetype to adopt. Brand archetypes come from Carl Jung’s work. Using them ensures we tap into something deeper than just the brand when designing.

The questionnaire included questions like:

  • Think your ideal client. What is their age?
  • What stage of life are they in? Are they college students? Married? Have kids? Retired?
  • What stage is their business in? Bootstrapped? Startup? Fortune 500? 3 employees? 100 employees?
  • What responsibilities do they handle at work?
  • Are they more likely to have a practical car or a Tesla?
  • Are they more likely to hire someone based on data or a gut feeling?

These questions helped me see what kind of mindset the clients were in and what brand personality would be appropriate to talk with them.

I also asked the client for a list of competitor websites (not to copy but to differentiate from) and brands they looked up to.

I learned their ideal client was an ambitious, logically-minded, and relationship/community-oriented affiliate marketer. I learned most of their competitors had out-of-touch branding—”traditional and tired casino image (palace, red carpets, luxury cars and other clichés à la James Bond)” while my client has always tried to bring out the fun, playful, games side of their niche, which is iGaming aka online casinos.

Learning about the brands they looked up to was informative too.

I like them a lot because I don’t come from a corporate background and never liked wearing suits.

With this information, and a feeling that the name Lonely Captain would sound moody if it was taking itself seriously, I made a case for the Jester as the brand archetype going forward.

For fun, joy and mischief, there’s no better archetype than the Jester. This is a great archetype to employ if a business wants its customers to enjoy themselves or be more spontaneous. The Jester gets away with being a bit irreverent because this archetype brings so much amusement to life.

I sent the client this write-up and a couples examples of brands with this personality archetype.

I studied the design elements often used to evoke a humorous mood and sent the clients live examples of each, asking them to share their thoughts on the possibility of using these as part of the brand. At this stage I was trying to figure out to what degree they wanted to be humorous. The Jester isn’t always laugh-out-loud funny.

  1. Wide range of colors (“rainbow”) (
  2. Joke-y copy (
  3. Cartoon elements (
  4. Silly display fonts (
  5. Pops of color (
  6. Lighthearted tone (
  7. Marquee (
  8. Big text (

Their answers helped me see that they wanted the look to be fun but stay toned down.

The logo concepts

From the get-go I felt the name of the business lent itself well to a mascot kinda logo. I created 3 options, each with a different story.

The first one is a cartoon-looking captain. He is sad and smoking a pipe. I imagine him alone looking into the distance but confident about the course of his ship.

The second option is a more serious-looking captain. He is also sad but his eyes are open and he is shedding a tear. The story behind this one is that he has a lot on his shoulders but he’s passionate about getting the job done right.

The third option is a captain that has been so lonely he’s going a little crazy. I think this one is a fun idea though visually it needs to be cleaned up a bit.

The client (who is great at giving feedback) picked the first option with this rationale:

The first captain brings a sense of playfulness with his funny mustache and potato head, but at the same time seems to be concentrating on the task at hand, with the blue color providing a sense of clarity and calmness, and like you said confidence (and needless to say, the blue fits perfectly the captain at sea theme).

The logo system

Because this was a digital company, I felt it was important to create a logo system for the brand.

While in the past having one consistent logo for printing on business cards was enough, nowadays there are so many different places a logo shows up. Basically a logo system a way to create variations on the logo so you can use different designs where appropriate but it still is the same logo in spirit. For example, the social media profile should have a square layout but the website will likely have a horizontal layout.

I created this the logo system which consists of 5 logos. You can see how one logo would be better on the website while another could be on a mug, but the brand is consistent.

The style guide

At this point, I wanted to make some rules for the brand so others designers would know how to work with it.

I designed a style guide that included the brand story, voice, logo system, typography, colors, and graphic elements. Although I can’t show it for the client’s privacy, take a peek at the cover.

The brand design was already showing itself to be fun and easy to work with.

The swag design

I’m not 100% happy with these designs—I learned here that although I put thought, heart, and lots of time into designs, sometimes (in this case, for swag design) it’s better for me to hire someone else to deliver. At the time I wasn’t doing this often but I do it more now with a few trusted freelance friends. Some things come out better this way.

I presented these concepts as just written ideas at first and designed them when the client was happy with the idea. I presented multiple ideas for each medium, i.e. there were several text options the client could have gone with for the water bottle including:

  • Ocean Waves
  • Just Add Water
  • All Good | Water
  • Water
  • Wavy
  • Elixir of Life
  • Water (in different languages)
  • H2-OH!
  • Drink Me
  • Water You Doing?
  • Do Water You Like
  • Earth Juice

The Lone Affiliate Manager mug was going to be a series for lone employees, meaning people who are the only ones with their role at a company. This was based off the ideal client questionnaire where I learned the target audience was companies with about 10 employees.

The Lucky mug was going to come in an Unlucky version too. My thinking was people could pick one depending on which resonates with them most. I imagine the entrepreneur types will like “Lucky” and more laid-back types will find the word “Unlucky” in a beautiful font funny. “Unlucky” also relates to “Lonely” pretty well, in a lighthearted self-disparaging sort of way, but the client decided not to go in that direction.

Countdown website

Lastly, I designed and built the launch countdown page. I wanted the page to memorable and engaging so people would come back, because when’s the last time you revisited a coming soon page? I placed the friendly captain right at top and coded an interactive fish.

The fish would follow your mouse on desktop and swim to where you tapped on mobile. If you tapped or hovered over the sky, the fish would jump out of the water, do a few spins, and dive back into the dark blue.

Working with the illustrator

Although this was technically a part of a separate project (for the full website) I also wanted to share how I worked with an illustrator to bring the brand to life. The images I was creating for the site were not telling the brand story properly. I illustrate but I like minimalist illustrations, so we decided to hire an illustrator so they could take the lead on that.

First, I found a reasonably-priced illustrator on Fiverr. By reasonably-priced I mean on the more expensive side as the client did not want to sacrifice quality. The reason I looked on Fiverr was because I wanted to get it done quickly so I searched for someone who was actively looking for work.

The illustrator ended up Astrid Prasetianti who is wonderfully talented and easy to work with. Her style was close to the one we wanted which featured fun, silly, a little exaggerated illustrations with thin to medium black outlines.

To help Astrid, I put together a moodboard, or a collage of relevant images for inspiration. The client reviewed this before it went out.

I provided a list of detailed ideas for her to work with as well.

My prompt for the homepage illustration: A happy captain on an island playing a trumpet and dancing. I think this is a good intro to the brand.

The illustration that came from it:

This illustration helped make the happy personality of the brand 100% compatible with the name!

Another prompt, this time for the Jobs page: Some sailors (including a woman or two) toasting, celebrating, drinking soda.

The illustration:

Visit Lonely Captain‘s site to see the rest of Astrid’s illustrations and how I designed the website! Even though there’s a part of me that wants to take all the credit for a project, I have learned to be more resourceful and hire others when it’s beneficial to the client.

That’s the end for the case study. I hope you enjoyed it. Feel free to leave questions or comments.